Products prepared by reacting hexamethylenetetramine with 1,3-dichloropropene are well-known and successful antimicrobial agents; U.S. Pat. No. 3,228,829. One product, cis-1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, commercially available as DOWICIL.RTM. (Registered trademark of The Dow Chemical Company) 200 and hereinafter referred to as "cis-compound" is used primarily in cosmetic and allied formulations. Another product, cis-,trans- mixtures of 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, commercially available under the DOWICIL.RTM. tradename, containing from about 50 to 99.5 percent cis-isomer and about 50 to 0.5 percent trans-isomer, is hereinafter referred to as "cis-,trans-compound". The cis-,trans-compound is used in commercial formulations such as, emulsifiable metal-cutting fluids; latex and emulsion paints; liquid floor polishes and floor waxes; glues and adhesives; coatings, sizings and printing colors for pulp and paper; and finishing solutions and printing pastes used by textile producers.
Although well-known and successful as anti-microbial agents, the cis- and cis-,trans-compounds may cause yellowing of the treated formulations. This yellowing seems to occur quickly, requiring only a few days to develop.
Certain amine compounds were found to inhibit color formation in aqueous solutions containing the cis- and cis-,trans-compounds. Polemenakos and Langer in U.S. Pat. No. 3,908,009 teach the use of amine compounds to stabilize solutions against discoloration. However it was found that the amines that work well in aqueous solutions did not work in the latex systems. It is desirable to prevent the yellowing of most compositions containing the aforesaid antimicrobial agents, especially in areas such as the latex and cosmetic industries.
This invention provides a novel composition of matter which utilizes the effective antimicrobial properties of the cis-compound and cis-,trans-compound and affords a non-yellowing formulation.